Category: 1192-21-8

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H7N3

3rd generation BrettPhos pre-catalyst (0.227 g, 0.25 mmol) was added to methyl i-(i((tert-butoxycarbonyl)amino)-3 -methoxypropan-2-yl)-4-(2-chloro-5 -methylpyrimidin-4- yl)-1H-pyrrole-2-carboxylate (1.1 g, 2.51 mmol), i-methyl-1H-pyrazol-5-amine (0.487 g, 5.01 mmol) and cesium carbonate (2.041 g, 6.27 mmol) in 1,4-dioxane (30 mL) at 25 °C under nitrogen. The resulting solution was stirred at 85 °C for 3 hours. The reactionmixture was poured into water (25 mL), extracted with EtOAc (3 x 50 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford crude yellow solid. The crude product was purified by flash silica chromatography, elution gradient 80 to 90percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl 1 -(1- ((tert-butoxycarbonyl)amino)-3 -methoxypropan-2-yl)-4-(5 -methyl-2-(( i-methyl-i H25 pyrazol-5-yl)amino)pyrimidin-4-yl)-1H-pyrrole-2-carboxylate (0.700 g, 55.9 percent) as a whitefoam. mlz: ES+ [M+H]+ 500.

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: pyrazoles-derivatives

Procedure NA mixture of an appropriate amine or aniline, respectively (1.0 mmol), an appropriate carbox- ylic acid (1.0 mmol), HBTU (1.0 mmol), a catalytic amount of 4-dimethylaminopyridine (DMAP), iV-ethyldiisopropylethylamine (1.25 mmol), and dry dichloromethane (2 mL) was stirred at room temperature for 12-48 h. The solvent was evaporated under reduced pressure. The residue was taken up with EtOAc (25 mL) and washed with 5 percent citric acid, water, saturated aqueous NaHCO3 solution, and brine. After drying (MgSO4), the solvent was removed under reduced pressure. The product was purified by preparative TLC, flash chromatography, or preparative HPLC. Purity was confirmed by 1H NMR and LC/ESIMS.For the synthesis of Example 145, gaseous ammonia was introduced into the reaction mixture. No additional amine base was applied.For the synthesis of Example 146, methylammonium chloride was applied as the amine, and the amount of amine base was increased to 2.5 mmol. For the synthesis of Example 147, dimethylammonium chloride was applied as the amine, and the amount of amine base was increased to 2.5 mmol.For the synthesis of Example 148, diethylamine was applied as the solvent. Therefore, no additional amine base was applied. For the preparation of 2-(nonyloxy)acetic acid (Intermediate 5) and 3-(octyloxy)propanoic acid (Intermediate 6), 12-(methylthio)dodecanoic acid (Intermediate 13), 12-(methyl- sulfonyl)dodecanoic acid (Intermediate 14), 10-(methylsulfonamido)decanoic acid (Intermediate 15), 4-aza-3-oxododecanoic acid (Intermediate 16), and l-dodecanoylpyrrolidine-3- carboxylic acid (Intermediate 17) see below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1192-21-8, its application will become more common.

Reference:
Patent; QUONOVA LLC; WO2009/77844; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7N3

[00205] Step 1 : 5-Amino-l -methyl- lH-pyrazole (6.25 g, 64.4 mmol) was dissolved in THF (120 ml) and treated with sodium hydride (3.51 g, 87.8 mmol). The reaction was heated to 35 C for 30 minutes and then treated with a dimethylformamide (“DMF”) solution (24 mL) of 4-bromo-2-fluoropyridine (10.3 g, 58.5 mmol). The reaction was heated to 50 C and stirred for 1 hour. The reaction was allowed to cool and treated with water, and the organics were concentrated. The residue was diluted with ethyl acetate and washed with water and brine. The organics were dried over Na2S04, filtered and concentrated. The material was purified on silica gel eluting with 30-100% ethyl acetate/hexanes followed by 25% methanoLDCM to afford 4-bromo-N-(l-methyl-lH-pyrazol-5-yl)pyridin-2-amine (6.55 g, 25.9 mmol, 44.2% yield).

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; COOK, Adam; GAUDINO, John; GUNAWARDANA, Indrani, W.; HICKEN, Erik, James; HUNT, Kevin, W.; LYON, Michael; METCALF, Andrew, T.; MOHR, Peter, J.; MORENO, David, A.; NEWHOUSE, Brad; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; GAZZARD, Lewis; SCHMIDT, Jane; DO, Steve; WO2015/103137; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1192-21-8, A common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 2 2-({5-Chloro-2-[(1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide A mixture of 2-[(2,5-dichloro-4-pyridinyl)amino]-N-methylbenzamide (100 mg, 0.338 mmol), 5-amino-1-methyl-1H-pyrazole (65.6 mg, 0.675 mmol), Cs2CO3 (220 mg, 0.675 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 61.8 mg, 0.068 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 48.8 mg, 0.084 mmol) was heated at 150° C. in a microwave oven for 30 min. The reaction mixture was filtered, and the filtrate was concentrated, and the resulting crude product was purified by reverse phase HPLC and the product was treated with 2 N HCl to give 34 mg of product as an HCl salt (24percent). LCMS (ES) m/z=357.1 (M+H); 1H NMR (400 MHz, methanol-d4) delta ppm 8.01 (s, 1H), 7.76-7.74 (m, 1H), 7.62-7.61 (m, 2H), 7.55 (d, J=2 Hz, 1H), 7.42-7.39 (m, 1H), 6.52 (s, 1H), 6.33 (d, J=2 Hz, 1H), 3.76 (s, 3H), 2.91 (s, 3H).

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADAMS, Jerry Leroy; Faitg, Thomas H.; Johnson, Neil W.; Lin, Hong; US2010/113475; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1192-21-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1192-21-8 name is 1-Methyl-1H-pyrazol-5-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To the solution containing the amine compound (A-1), 700 mL of methanol was added. While stirring the obtained solution at an internal temperature of 5 ° C., To this solution, 120 g of an 85percent by mass aqueous solution of phosphoric acid (H 3 PO 4) (1.0 mol as H 3 PO 4) was added dropwise. By dropwise addition, Crystals precipitated. Precipitated crystals were collected by filtration, 111 g of crystals (slightly yellow to white crystals) of the organic amine salt (I-beta-2) were obtained (yield 57percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; Mikoshiba, Atsushi; (36 pag.)JP2017/19914; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1192-21-8, COA of Formula: C4H7N3

Under nitrogen a solution of methyl 4-bromo-l-(3-methoxyphenyl)-lH-pyrazole-3- carboxylate (600 mg, 1.928 mmol, 1.00 equiv), l-methyl-lH-pyrazol-5-amine (563 mg, 5.797 mmol, 1.00 equiv), t-BuXPhos (82 mg, 0.193 mmol, 0.10 equiv), 3rd Generation t-BuXPhos precatalyst (154 mg, 0.194 mmol, 0.10 equiv), t-BuONa (279 mg, 2.903 mmol, 1.50 equiv) in 1 ,4-dioxane (12 mL) was irradiated with microwave radiation for 90 min at 90 °C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (1 : 1) to give the title compound (425 mg, 70percent) as a yellow solid. LC-MS (ES, m/z): 314 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1192-21-8, Recommanded Product: 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methylpyridin-3-yl)methyl)-3 ,4- dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (118 mg, 0.31 mmol), i-methyl-i H-pyrazol-5 -amine (33.0 mg, 0.34 mmol), cesium carbonate (201 mg, 0.62 mmol) and BrettPhos 3rd generation pre-catalyst (14.01 mg, 0.02 mmol) were suspended in tert-butanol (5 mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18 hours under nitrogen. The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueousportion was washed with ethyl acetate (50 mL) and the combined organics were dried (sodium sulfate) and concentrated in vacuo to a brown gum (198 mg). The solid was taken up in DMSO (5 mL) and filtered. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (3 S)-3 -methyl-7-(5 -methyl-2-(( i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methylpyridin-3 -yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (74.0 mg,54.1 percent) as a white solid. ?H NMR (400 MHz, DMSO, 30 °C) 1.14 (3H, d), 2.32 (3H, s),3.68 (3H, s), 3.81 (1H, d), 4.16 – 4.27 (2H, m), 4.34 (1H, dd), 5.12 (1H, d), 6.26 (1H, d),7.20 (1H, dd), 7.27 (1H, d), 7.33 (1H, d), 7.58 – 7.7 (2H, m), 8.23 (1H, s), 8.35 (1H, d),9.06 (1H, s). mlz: ES+ [M+H]+ 442.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5 -methylpyrimidin-4-yl)-3 -methyl-2-((3 -methylpyrazin-2-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (125 mg, 0.33 mmol), 1-methyl-i H-pyrazol5-amine (34.9 mg, 0.36 mmol), cesium carbonate (213 mg, 0.65 mmol) and BrettPhos 3rdgeneration pre-catalyst (14.80 mg, 0.02 mmol) were suspended in tert-butanol (5 mL) andde-gassed for 10 minutes. The reaction was heated to 80 °C for 18 hours under nitrogen.The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueous portion was washed with ethyl acetate (50 mL) and the combined organics were dried (sodium sulfate) and concentrated in vacuo to a brown gum which was taken up in DMSO(5 mL) and filtered. The crude product was purified by preparative HPLC (Waters XBridge Prep Ci8 OBD column, Sji silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford (3S)-3-methyl-7-(5-methyl-2- ((i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((3 -methylpyrazin-2-yl)methyl)-3 ,4-dihydropyrrolo[i,2-a]pyrazin-i(2H)-one (97 mg, 67.0 percent) as a white solid. ?H NMR(500 MHz, DMSO, 30 °C) 1.43 (3H, d), 2.58 – 2.6 (3H, m), 2.83 (3H, s), 3.94 (3H, s), 4.15- 4.25 (iH, m), 4.44 (iH, dd), 4.55 – 4.67 (2H, m), 5.60 (iH, d), 6.52 (iH, d), 7.50 (iH, d),7.59 (iH, d), 7.90 (iH, d), 8.49 (iH, d), 8.64 – 8.71 (2H, m), 9.33 (iH, s). mlz: ES+[M+H]+ 443.

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1192-21-8, A common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

in two screw-top glass pressure vessels, split and combine the following amounts in two equal portions 2-(2-chioro-4-pyridyi)-5-(2-nethoxyethyi)-6,6-dimethyi-thieno[2,3- c]pyrroi-4-one (13 g, 38.59 mmol), 1-methyi-5-aminopyrazole (11.245 g, 115.78 mmoi),cesium carbonate (37.724 g, 115.78 mrnol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (2.010 g, 3.47 mmoi), paiiadium(ii)acetate (520 mg, 2.32 nmoi) and 1,4-dioxane (350 mL). Seal each vessel and heat at 110 °C overnight.Dilute the reaction mixture with 10percent MeOH in DCM (2 L) and wash the resulting solution with saturated NaC1. Back extract the aqueous solution with DCM and combinethe organic solutions. Dry the combined solutions over a mixture of an hyous sodium sulfate and aithydrous magnesium sulfate, filter and concentrate the filtrate under reduced pressure. Purify by silica gel chromatography by loading the residue onto a 260 g loading coiunm with DCM and then eluting the loading coiunm onto a 750 g silica gel column with a gradient of 60-100percent of 10percent MeOH in EtOAc in hexane to yield the titlecompound 8.4 g (55percent). MS rn/z): 398 (M+i).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ELI LILLY AND COMPANY; CORTEZ, Guillermo S.; JOSEPH, Sajan; MCLEAN, Jonathan Alexander; MCMILLEN, William T.; RODRIGUEZ, Michael John; ZHAO, Gaiying; (70 pag.)WO2016/106009; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 1-Methyl-1H-pyrazol-5-amine

3rd Generation BrettPhos precatalyst (22.95 mg, 0.03 mmol) was added to 2-(2-chloro-5- methylpyrimidin-4-yl)-7-((6-(difluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 51; 205 mg, 0.51 mmol), 1-methyl- lH-pyrazol-5-amine (123 mg, 1.27 mmol) and CS2CO3 (330 mg, 1.01 mmol) in 1,4- dioxane (8 mL) at 25°C under nitrogen and the resulting mixture was stirred at 100 °C for 8 hours. The solvent was then removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 6percent MeOH in DCM. Compound containing fractions were evaporated to dryness to afford a yellow residue. This residue was purified further by preparative HPLC (XSelect CSH Prep C18 OBD column, 5mu silica, 19 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.03percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 7-((6-(difluoromethyl)pyridin-2- yl)methyl)-2-(5-methyl-2-((l-methyl-lH-pyrazol-5-yl)amino)pyrimidin-4-yl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 15; 122 mg, 51.8percent) as a white solid. H NMR (400 MHz, DMSO, 20°C) delta 2.50 (3H, s), 3.70 (3H, s), 3.87 – 3.95 (2H, m), 4.42 – 4.50 (2H, m), 4.87 (2H, s), 6.30 (1H, d), 6.95 (1H, t), 7.33 (1H, d), 7.61 (2H, t), 7.94 (1H, s), 8.00 (1H, t), 8.32 (1H, s), 9.24 (1H, s). m/z (ES+), [M+H]+ = 466.

The synthetic route of 1-Methyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics